4-(2,3-bis-nitrooxypropyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2,3-bis-nitrooxypropyl)phenol
• 英文别名: [1-(4-Hydroxyphenyl)-3-nitrooxypropan-2-yl] nitrate
• 化学式: C₉H₁₀N₂O₇
• 分子量: 258.188
• InChiKey: PBDZCCAXRGGKLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(2,3-bis-nitrooxypropyl)phenol 在 吡啶 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.25h， 生成 (4-(2,3-bis(nitrooxy)propyl)phenoxycarbonyl)oxymethyl 2-(acetyloxy)benzoate
  参考文献：
  名称：

  New Nitric Oxide or Hydrogen Sulfide Releasing Aspirins

  摘要：

  A new series of (((R-oxy)carbonyl)oxy)methyl esters of aspirin (ASA), bearing nitric oxide (NO) or hydrogen sulfide (H2S) releasing groups, was synthesized, and the compounds were evaluated as new ASA co-drugs. All the products were quite stable in buffered solution at pH 1 and 7.4. Conversely, they were all rapidly metabolized, producing ASA and the NO/H2S releasing moiety used for their preparation. Consequent on ASA release, the compounds were capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma (PRP). The simple NO/H2S donor substructures were able to relax contracted rat aorta strips, with a NO- and H2S-dependent mechanism, respectively, but they either did not trigger antiaggregatory activity or displayed antiplatelet potency markedly below that of the related co-drug. The new products might provide a safer and improved alternative to the use of ASA principally in its anti-inflammatory and antithrombotic applications.

  DOI：

  10.1021/jm2004514
• 作为产物：
  描述：

  对烯丙基苯酚 在 四氢吡咯 、 4-二甲氨基吡啶 、 碘 、 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.33h， 生成 4-(2,3-bis-nitrooxypropyl)phenol
  参考文献：
  名称：

  NO供体酚：具有抗氧化剂和血管舒张特性的新型产品。

  摘要：

  描述了新型能够释放一氧化氮的酚类的抗氧化剂和血管扩张剂的合成和研究。这些产品是通过共生方法设计的，使用了选定的苯酚以及选定的硝基氧基和呋喃喃NO供体作为参考模型。通过检测在大鼠肝细胞的微粒体膜中存在的亚铁盐/抗坏血酸诱导的脂质的自氧化中产生的2-硫代巴比妥酸反应性物质（TBARS），可以评估杂化产物的抗氧化活性。在与去氧肾上腺素预收缩的大鼠主动脉条上评估血管舒张活性。一些产品（13、35、37、60-62、64）主要表现为血管扩张剂，而其他产品则表现为抗氧化剂（24、32、72），并且两种特性在19、41和68中相对平衡。

  DOI：

  10.1021/jm0510530

文献信息

• NITRIC OXIDE DONOR NEPRILYSIN INHIBITORS
  申请人：Mammen Mathai

  公开号：US20130323271A1

  公开（公告）日：2013-12-05

  In one aspect, the invention relates to compounds having the formula: where R 1 , R 2 , R 3 , R 7 , R 8 , Z, X, b, and c are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds are nitric oxide donors and have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.

  在一方面，本发明涉及具有以下公式的化合物：其中R1、R2、R3、R7、R8、Z、X、b和c按说明书定义，或其药用可接受的盐。这些化合物是氧化氮供体并具有中性内肽酶抑制活性。在另一方面，本发明涉及包含此类化合物的药物组合物；使用此类化合物的方法；以及制备此类化合物的过程和中间体。
• US9045443B2
  申请人：——

  公开号：US9045443B2

  公开（公告）日：2015-06-02
• New Nitric Oxide or Hydrogen Sulfide Releasing Aspirins
  作者：Loretta Lazzarato、Konstantin Chegaev、Elisabetta Marini、Barbara Rolando、Emily Borretto、Stefano Guglielmo、Sony Joseph、Antonella Di Stilo、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm2004514

  日期：2011.8.11

  A new series of (((R-oxy)carbonyl)oxy)methyl esters of aspirin (ASA), bearing nitric oxide (NO) or hydrogen sulfide (H2S) releasing groups, was synthesized, and the compounds were evaluated as new ASA co-drugs. All the products were quite stable in buffered solution at pH 1 and 7.4. Conversely, they were all rapidly metabolized, producing ASA and the NO/H2S releasing moiety used for their preparation. Consequent on ASA release, the compounds were capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma (PRP). The simple NO/H2S donor substructures were able to relax contracted rat aorta strips, with a NO- and H2S-dependent mechanism, respectively, but they either did not trigger antiaggregatory activity or displayed antiplatelet potency markedly below that of the related co-drug. The new products might provide a safer and improved alternative to the use of ASA principally in its anti-inflammatory and antithrombotic applications.
• NO-Donor Phenols:  A New Class of Products Endowed with Antioxidant and Vasodilator Properties
  作者：Donatella Boschi、Gian Cesare Tron、Loretta Lazzarato、Konstantin Chegaev、Clara Cena、Antonella Di Stilo、Marta Giorgis、Massimo Bertinaria、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm0510530

  日期：2006.5.1

  The synthesis and study of the antioxidant and vasodilator properties of a new class of phenols able to release nitric oxide are described. The products were designed through a symbiotic approach using selected phenols and selected nitrooxy and furoxan NO-donors as reference models. The antioxidant activities of the hybrid products were assessed by detecting the 2-thiobarbituric acid reactive substances

  描述了新型能够释放一氧化氮的酚类的抗氧化剂和血管扩张剂的合成和研究。这些产品是通过共生方法设计的，使用了选定的苯酚以及选定的硝基氧基和呋喃喃NO供体作为参考模型。通过检测在大鼠肝细胞的微粒体膜中存在的亚铁盐/抗坏血酸诱导的脂质的自氧化中产生的2-硫代巴比妥酸反应性物质（TBARS），可以评估杂化产物的抗氧化活性。在与去氧肾上腺素预收缩的大鼠主动脉条上评估血管舒张活性。一些产品（13、35、37、60-62、64）主要表现为血管扩张剂，而其他产品则表现为抗氧化剂（24、32、72），并且两种特性在19、41和68中相对平衡。